Copper compounds of orthooxyazo dyestuffs and a process of making same.



. N0 Drawing.

BERTI-IOLD WUTH AND CARL JAGERSPACI-IER, or BASEL, swITznnLANmAssIe'Nons T0 soo E'rY or CHEMICAL INDUSTRY IN BASLE, or nAsE swIrznnLAND.ME

COPPER COMPOUNDS or ORTHOOXYAZO DYESTUFFS AND A rnoor issi'or To all whom it may concern:

Be it known that we, BERTHOLD VVUTH, chemist, a subject of the King of Great Britain, and CARL JAGERSPACHER, chemist, a citizen of the Swiss Republic, both residents of Basel, Switzerland, have invented New Copper Compounds of Orthooxyazo Dyestuffs and Processes of Making Same, of which the following is a full, clear, and exact specification.

In the United States application for Letters Patent,Ser. No. 43313, filed August 3, 1915, is described the production of new well defined copper compounds of orthooXyazo dyestuffs, which are soluble in water. We have now found, that the orthooxydiazo dyestuffs derived from the polycyclic ring systems containing a CH group able to combine with a diazo group,-as for instance diketohydroinden perinaphth rdandion.

CH2 0 6 to 3-oXy-1-thionaphthen ketocumaran l l indoxyl l Specifieation of Letters Patent.

Application filed October 7, 1915.

Patented July 1'7, 191?.

Serial No. 54,504. i

copper compounds dissolve in concentrated sulfuric acid to deep colored solutions and water to intense colored solutions which do sodium carbonate or of soda lye.

not change their coloration on addition of The preparation of the heretofore unknown dyestuffs from orthodiazophenolden ivates or orthodiazonaphthol derivates and perinaphthindandion, ketocumaran, indoxyl,

etc., takes place in the usual way by com .bining the orthooxydiazo compounds with the said components in an alkaline solution f as it is illustrated by'the following examples:

Example 1: 24 parts of 1 2 l-aminonaphtholsulfonic acid are diazotized in the known manner and mixed with a soda alkaline solution of 20 parts perinaphthindan dion dissolved in 1 1 parts of soda lye of 3. per cent. The combination being achieved." the dyestulf is separated, pressed and dried It dissolves in water to brown-red and in concentrated sulfuric acid to blue solutions and dyes wool in an acid bath violet-brown shades. 1

The preparation of the copper compound of the said orthooxyazo dyestuffs is illus trated by the following examples:

Example 2: 24: parts of the dyestuflf obtained, according to Example 1, from 1 :23- diazonaphtholsulfonic acid and perinaphthindandion are dissolved in 1000 parts hot water at 80 C. and into the thus obtained solution is poured a solution of 13 parts of copper sulfate in 50 parts water.

The copper compound separates at once as a black precipitate. After neutralization of the freed sulfuric acid with sodium carbonate, the new'copper compound is isolated by filtration, pressed and dried. It dyes wool in an acid bath brown-red shades very.

fast to washing and to light. a 1

Example 3": 21 parts of the dyestuff resulting from the 1:2:4-diazonaphtholsulfonic acid and oxythionaphthen are. dissolved in 00 parts Water and to this solution shades parent washing,

while the orthooxyazo dyestufi materia tints.

1 yields value alkali and li ht,

employed as less roseate 10 The following tabular exhibit relates to several copper compounds cording to the invention:

obtainable ac- Dyestufi resulting from Dyeing ol the sodium salt from acid Dyeing of the co bath on WOOL rsnltlromac d The diazo derivate of Andl} 011 W001, 0H Diketohydroinden..... Yellow-brown Red-brown.

OH Indoxyl Red-brown Violet.

/NHg

fi-Methylketocumaran Yellow Violet. NH; CH 0:

\ZHQ. oo v SOaH Diketohyd.roinden Red-brown Violet.

Diketohydroinden Orange Red-brown. il,

' Perinaphthindandion Yellow-orange Red-brown.

Ierlnaphthindandicn Violet-brown. Bordeaux. (I OH OaH Dyestufl making (romv v Dyein ofthe sodiumsaitfrohiacid 'j the persaltl'romacld "Ihedmwdenvate of- A bath on wool botlyonwool.

OH Perinaphthindandion Red-orangeuU Yel lopf btown. GQ0E NH (:H B-Oxy-l-thionaphthexi! Red-brown Red vi0le OH 3-Oxy -1-thi0naphthen Red-brown Violet.

so ny NH;

S-Oxy-l-thionaphthen Roseateun Pureviolet-blue.

11111 fi-Methylketocumaran Red-brown Blue.

on o

NH: 3-0xy-1-thjonaphthen Roseate Black-vioiet.

a ox d-tmona hthn Brown-violet Violet-black.

What we claim. is: 7 IL The described process for the manufac- We of new copper compounds of ortloooKym-zo dyestufis, soluble in Water,'cons1s t- 5 img in treating with copper compounds m taming a CH a diam-group. 4

2. The described process for a water medium the orthooxyazo dyestufis derived from polycyclic ring systems conj group able to combine W1th the manufac- 10 ture of new copper compounds of orthooxyazo dyestufi's, soluble in water, consist- 3. As new products the described copper compounds of orthooxyazo dyestuffs, which contain an azo group combined to a CH group of a polycyclic ring system, aresoluble in water, from which the copper can not be precipitated by sodium carbonate, soda lye and ammonia. and which constitute red, brown, violet and blue to black powders, dissolving in concentrated sulfuric acid to deep colored solutions and in Water to intense colored solutions which do not change their coloration on addition of sodium carbonate or soda lye and. from which the animal fibers as wool, silk and leather, straw and wood-hast are dyed, according the methods used for acid dyestufis, red, brown, violet and blue to black tints show-, ing without any further treatment a, very good fastness to washing and to light.

In Witness whereof we have hereunto signed our names this 11th day of September, 1915, in the presence of two subscribing witnesses.

DR. BERTHOLD VVUTH. DR. CARL JAGERSPACHER. Witnesses:

ARNOLD ZUBER, AMAND BITTER. 

